10 Cool Things To Do in the Massachusetts Berkshires for Kids

The Berkshires for kids? Really? The Berkshires MA is mostly associated with beautiful resorts and arts and culture. Can you really find cool things to do in the Berkshires with kids that everyone in the family will enjoy? We think there are plenty of Berkshires things to do with kids especially for an outdoorsy family. Whether you have hardcore outdoor enthusiasts who like to hike Berkshires mountains or take in the view on the laid back Hoosac Valley Train, the Berkshires MA is great for a family vacation. 

10 Things to do in the Berkshires with Kids 

In the Berkshires, kids will get off their screens and enjoy nature. Frankly, they will have to – pretty much all the things to do in the Berkshires with kids are in the great outdoors.

Norman Rockwell Museum

Boasting the world’s most extensive collection of Norman Rockwell paintings, this museum is a nostalgic version of an America that never existed. There’s even an audio tour of the museum designed for children and families to help young visitors have fun viewing the artwork. 

 Berkshire Botanical Garden 

The 15 acres of the Berkshire Botanical Gardens are a great place to go for an afternoon walk or a picnic lunch. There is also a charming children’s garden which has fun things to explore like a fairy garden and a little house. We learned a lot about plants and wildlife indigenous to the area while also enjoying an afternoon out.

Bash Bish Falls State Park 

Home to the highest single-drop waterfall in the state, this Massachusetts state park is excellent for hiking, picnics, and great family photos for your Berkshires family vacation. 

Like many children, my kids have never seen rocks that they didn’t want to clamber over. Wet and slippery? Even better.

You are no longer allowed to go into the Bash Bish Falls themselves but the streams running into the falls are full of water, mud and rocks to explore.

Mt Greylock 

Massachusetts’s highest peak is a beautiful place to visit, particularly in the fall when the autumn leaves blanket the mountain in bright colors. Mt Greylock is both a state and a national park in Massachusetts.

Depending on how adventurous your kids are, you can hike up to the top of the mountain, which offers views up to 90-mile away on a clear day.

If you want to hike Berkshires less strenuously, then you can drive to the top of Mt Greylock for the same spectacular views. This drive is one of the most scenic Massachusetts’ drives as well. There are small walking paths at the top of Mt Greylock.

Magic Wings Butterfly Conservatory Garden 

The 8,000 square feet of the Magic Wings Conservatory can take you on a tropical adventure, even in the Berkshires MA. It’s similar in set up to other butterfly gardens, and there’s a gift shop and food court to make a full day out of your visit. 

Windy Hill Farm 

The Berkshires are known for their farm-to-table food scene and amazing gardens. You’ll get to see it all first-hand at the Windy Hill Farm in Great Barrington, where you can pick apples or blueberries in season and tour the garden center.

Jiminy Peak 

If you’re visiting the Berkshires with kids during a New England winter, Jiminy Peak is the place to go. Come for a day of skiing and snowboarding, or stay at the resort for a more immersive experience. There are classes available for beginner skiers. 

Jiminy Peak is also fun to visit in the summer thanks to mountain bike trails, an adventure park, and elevated climbing courses of varying difficulties. 

Hoosac Valley Train 

Taking a scenic railway ride through the Berkshires MA is a great activity that kids of all ages will enjoy. If you’re traveling during the holidays for your Berkshires vacation, be sure to see if there are any fun events going on at the Hoosac Valley Train, like spooky Halloween rides or festive Christmas train experiences. 

Hancock Shaker Village 

For an interesting look at some of the history of the Berkshires, you can visit the Hancock Shaker Village, a former Shaker community. The area functions as a living museum, historic landmark, and working farm, where visitors can learn about the Shaker lifestyle and belief system. 

Ashuwillticook Rail Trail 

We love converted rail tracks for easy cycling options for the whole family. The Ashuwillticook Trail is one of these converted rail tracks creating an accessible scenic route through the Berkshires.

The ten-foot-wide path is paved, so you can take the kids on a bike ride or walk to view the beautiful scenery of the area. During the fall, the path is particularly beautiful, thanks to the brightly colored autumn leaves.

Places to Stay in the Berkshires 

The Berkshires is a great place to take a break from the rush of daily life. The mountain towns of western Massachusetts offer endless outdoor activities as well as a great art scene. Traveling to the Berkshires for kids can be lots of fun starting with your Berkshires family resort. 

For a Berkshires family vacation, these are the places to stay in the Berkshires we would recommend:

• One of the Berkshire’s best-known guesthouses, the Red Lion Inn Stockbridge offers a fun and comfortable experience for the whole family. In addition to the main inn, you can rent village houses which are suitable for families. There is a little pool on site as well which kids will like.
• Blantyre is a Gilded Age mansion in Lenox which is part of the luxury Relais & Chateaux brand – expect it to be expensive and exquisite Berkshires family resort. Blantyre also has cottages to rent that are suitable for families. Children over the age of 8 can dine at its Cafe Boulud (part of the international empire of Michelin-starred chef Daniel Boulud who hails from Lyon in France)
• For a more casual experience, Porches Inn in North Adams offers all the comforts of home, such as kitchens and fireplaces, creating a perfect blend of retro charm and modern amenities. At this Berkshires family resort, you will be staying in town in the renovated accommodation of the area’s former mill workers.

Map of Things To Do in the Berkshires, Kids Version

For your Berkshires vacation planning, here are where you can find a handy map of recommendations for what to do in the Berkshires with kids as well as the places to stay in the Berkshires we suggest.

SPREAD THE WORD! PIN THIS TO YOUR TRAVEL PINTEREST BOARDS FOR FUTURE REFERENCE! 

This site generates income via partnerships with carefully-curated travel and lifestyle brands and/or purchases made through links to them at no extra cost to you. More information may be found on our Privacy Policy.